Double training this weekend, because of the holiday. i had to travel to Mistress' flat wearing my bra, panties and stockings under a pink t shirt and my tight jeans.

Mistress lets me in and orders me to strip down to my frillies (thats what she calls them) and then join Craig and her in the sitting room. She is still in her nightie, and he is only wearing boxers.  "We had a great night of sex together, Jessica" she said/ "Craig is a real man and can give me a proper fuck. Not like you, little sissy. Now kneed down".

 i did as i was told.

"On all fours!" i obey. "Ass in the air!"

i can hear her behind me, taking something out of a plastic wrapper. She shoved the object under my nose - its a black plastic plug.

"This is for the next step in your training, readying your sissy pussy for use. Craig, could you help me?"

She pushed my head down and i felt Craig lower my panties and part my buttocks. Then a shock of pain and discomfort as the plug slipped into me, feelings  which passed as Craig replaced my panties.

"There, little sissy. Not so bad is is? You are feeling what every girl feels; the sensation of being fucked. Soon it will be a real cock in there. Now up!"

Craig helped me to my feet. It felt funny standing there with a hard plug in my ass. i realised i had taken  an important step to sissydom, and secretly quite liked the feeling.

Mistress left the room to fetch something, leaving Craig to get me used to walking while plugged, with a lot of unnecessary rubbing against my body, never letting me forget  his hard cock inside his boxers.Mistress returned with a pair of pink high heeled shoes, and i had to hold  onto Craig as she helped put them on. i spent some time learning how to walk in heels, with the plug in my ass.

Later i had to show i had learned my lesson about cocksucking, and Caig gave me another spanking.

i have to wear panties and stockings to work, and put my plug in when i am at home. i may be called for further training today.